UPDATE: The state Supreme Court has issued a stay of Friday’s execution of Cal Coburn Brown after a state clemency board voted 2-2 to stay the execution. The clemency board’s recommendation moved to Gov. Gregoire, but the Supreme Court issued its stay before the governor issued an opinion.

Convicted killer Cal Coburn Brown has lost another appeal in his effort to stay out of the death chamber and is now hoping that the governor or the state Supreme Court will intervene.

Barring a last-minute stay, Brown is scheduled to be executed at 12:01 a.m. Friday. His would be the first execution in Washington since 2001.

Brown, 50, was convicted by a King County jury in the 1991 slaying of Holly Washa, 22, near Seattle-Tacoma International Airport.

On Wednesday, Thurston County Superior Court Judge Chris Wickham refused Brown’s motion challenging the state’s right to administer lethal injection. His attorneys had asked for a stay so Brown could join similar challenges by death-row inmates Darold Ray Stenson and Jonathan Gentry scheduled to be heard in Thurston County in May, said Seattle defense attorney Jeff Ellis.

King County Prosecuting Attorney Dan Satterberg called Brown “one of the worst offenders we’ve ever seen in King County.”

“He got a very fair assessment,” Satterberg said. “Every issue has been raised, and now it’s time to carry out the sentence.”

According to court documents, Brown’s attorneys argued that the state hasn’t the authority to administer the combination of three drugs used in lethal injection. The first drug is supposed to cause the prisoner to lose consciousness and prevent pain. The second causes muscle paralysis so the prisoner stops breathing and the third stops the heart.

Because of the paralysis, defense attorneys argued in the court filings, it is impossible to tell whether the prisoner is experiencing pain.

Defense attorneys have argued that the injection cocktail should be administered by a physician or a nurse anesthesiologist. The Department of Corrections uses a medical professional, not necessarily a doctor, on the team to give the drugs

Ellis said the defense is appealing Wednesday’s ruling to the state Supreme Court and is asking Gov. Chris Gregoire to issue a reprieve.

“A judge has said there is a real prospect that the imposition of the death penalty based upon the current protocols will cause undue suffering,” said Ellis. He said the judge’s ruling “defies rational explanation.”

Washa’s family wrote a letter to the Thurston court, urging Brown’s execution.

“This is something none of us can forget and it haunts us every day,” it said.

In May 1991, Brown carjacked Washa at knife point near Sea-Tac Airport, and forced her to write checks to him and tried to cash them.

He then took her to a hotel, raped and tortured her, according to prosecutors. He slashed and stabbed her several times and left her body in the trunk of her car.

Brown was caught after he kidnapped and raped another woman in California, according to prosecutors. She was able to call police.